IE42660B1 - Process for the preparation of the 0,0-dimethyl-0-(2,2-dichlorovinyl) ester and the 0,0-diethyl-0-(2,2-dichlorovinyl) ester of thionophosphoric acid - Google Patents
Process for the preparation of the 0,0-dimethyl-0-(2,2-dichlorovinyl) ester and the 0,0-diethyl-0-(2,2-dichlorovinyl) ester of thionophosphoric acidInfo
- Publication number
- IE42660B1 IE42660B1 IE579/76A IE57976A IE42660B1 IE 42660 B1 IE42660 B1 IE 42660B1 IE 579/76 A IE579/76 A IE 579/76A IE 57976 A IE57976 A IE 57976A IE 42660 B1 IE42660 B1 IE 42660B1
- Authority
- IE
- Ireland
- Prior art keywords
- ester
- dichlorovinyl
- alkali metal
- diethyl
- dimethyl
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims abstract description 22
- 150000002148 esters Chemical class 0.000 title claims description 36
- 238000000034 method Methods 0.000 title claims description 32
- 238000002360 preparation method Methods 0.000 title claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 51
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000000203 mixture Substances 0.000 claims abstract description 16
- -1 C2P Thiophosphate esters Chemical class 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 8
- 239000003960 organic solvent Substances 0.000 claims abstract description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 7
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims abstract description 7
- 150000008041 alkali metal carbonates Chemical class 0.000 claims abstract description 7
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 6
- 239000004480 active ingredient Substances 0.000 claims abstract description 5
- 230000000749 insecticidal effect Effects 0.000 claims abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 24
- 239000003085 diluting agent Substances 0.000 claims description 12
- 241000238631 Hexapoda Species 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 7
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 6
- 239000004094 surface-active agent Substances 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical group C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000002904 solvent Substances 0.000 abstract description 11
- 239000003795 chemical substances by application Substances 0.000 abstract description 5
- 150000005690 diesters Chemical class 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 150000003580 thiophosphoric acid esters Chemical class 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 4
- 241001124076 Aphididae Species 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 241000721621 Myzus persicae Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 241000500437 Plutella xylostella Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical class OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- TYQTYRXEMJXFJG-UHFFFAOYSA-N phosphorothious acid Chemical compound OP(O)S TYQTYRXEMJXFJG-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 241001425390 Aphis fabae Species 0.000 description 2
- 241000387321 Aspidiotus nerii Species 0.000 description 2
- 241001327638 Cimex lectularius Species 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 241000483001 Euproctis chrysorrhoea Species 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- 241000255896 Galleria mellonella Species 0.000 description 2
- 241001251909 Hyalopterus pruni Species 0.000 description 2
- 241000721715 Macrosiphum Species 0.000 description 2
- 241000255685 Malacosoma neustria Species 0.000 description 2
- 241000810465 Myzus cerasi cerasi Species 0.000 description 2
- 241001491877 Operophtera brumata Species 0.000 description 2
- 241000255969 Pieris brassicae Species 0.000 description 2
- 241000722238 Pseudococcus maritimus Species 0.000 description 2
- 241000125167 Rhopalosiphum padi Species 0.000 description 2
- 241000256251 Spodoptera frugiperda Species 0.000 description 2
- 241001414989 Thysanoptera Species 0.000 description 2
- 241001238451 Tortrix viridana Species 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- BNKAXGCRDYRABM-UHFFFAOYSA-N ethenyl dihydrogen phosphate Chemical class OP(O)(=O)OC=C BNKAXGCRDYRABM-UHFFFAOYSA-N 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 241000253994 Acyrthosiphon pisum Species 0.000 description 1
- 241000218475 Agrotis segetum Species 0.000 description 1
- 241000449794 Alabama argillacea Species 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- 241000254137 Cicadidae Species 0.000 description 1
- 241001415288 Coccidae Species 0.000 description 1
- 241001465977 Coccoidea Species 0.000 description 1
- 241001479447 Coccus hesperidum Species 0.000 description 1
- 241001094913 Cryptomyzus Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000289763 Dasygaster padockina Species 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 241001581006 Dysaphis plantaginea Species 0.000 description 1
- 241001425477 Dysdercus Species 0.000 description 1
- 241001425472 Dysdercus cingulatus Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000630736 Ephestia Species 0.000 description 1
- 241000122098 Ephestia kuehniella Species 0.000 description 1
- 241000239245 Euscelis Species 0.000 description 1
- 241000258937 Hemiptera Species 0.000 description 1
- 241001659688 Hercinothrips femoralis Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- 241000721703 Lymantria dispar Species 0.000 description 1
- 241000555303 Mamestra brassicae Species 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 241000961933 Nephotettix virescens Species 0.000 description 1
- 241001548358 Parapiesma quadratum Species 0.000 description 1
- 241000690748 Piesma Species 0.000 description 1
- 241001097374 Pselliopus cinctus Species 0.000 description 1
- 241000722249 Rhodnius prolixus Species 0.000 description 1
- 235000001537 Ribes X gardonianum Nutrition 0.000 description 1
- 235000001535 Ribes X utile Nutrition 0.000 description 1
- 235000016919 Ribes petraeum Nutrition 0.000 description 1
- 244000281247 Ribes rubrum Species 0.000 description 1
- 235000002355 Ribes spicatum Nutrition 0.000 description 1
- 241001402072 Sappaphis Species 0.000 description 1
- 241000985245 Spodoptera litura Species 0.000 description 1
- 241001414831 Triatoma infestans Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 241001466337 Yponomeuta Species 0.000 description 1
- 241000064240 Yponomeuta padellus Species 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- AYKVWLVCPVEZHW-UHFFFAOYSA-N ethenoxy-dihydroxy-sulfanylidene-$l^{5}-phosphane Chemical class OP(O)(=S)OC=C AYKVWLVCPVEZHW-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- LVFUWJLIDMSANU-UHFFFAOYSA-N methoxy(methylsulfanyl)phosphinous acid Chemical compound COP(O)SC LVFUWJLIDMSANU-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000002927 oxygen compounds Chemical class 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing acyclic or cycloaliphatic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/173—Esters of thiophosphoric acids with unsaturated acyclic alcohols
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Biochemistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752512177 DE2512177A1 (de) | 1975-03-20 | 1975-03-20 | Verfahren zur herstellung von o,o- dimethyl- bzw. o,o-diaethyl-o-(2,2- dichlorvinyl)-thionophosphorsaeureester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE42660L IE42660L (en) | 1976-09-20 |
| IE42660B1 true IE42660B1 (en) | 1980-09-24 |
Family
ID=5941884
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE579/76A IE42660B1 (en) | 1975-03-20 | 1976-03-19 | Process for the preparation of the 0,0-dimethyl-0-(2,2-dichlorovinyl) ester and the 0,0-diethyl-0-(2,2-dichlorovinyl) ester of thionophosphoric acid |
Country Status (34)
| Country | Link |
|---|---|
| JP (1) | JPS51115422A (tr) |
| AT (1) | AT338289B (tr) |
| AU (1) | AU504691B2 (tr) |
| BE (1) | BE839712A (tr) |
| BG (1) | BG27237A3 (tr) |
| BR (1) | BR7601678A (tr) |
| CA (1) | CA1058631A (tr) |
| CH (1) | CH601330A5 (tr) |
| CS (1) | CS191211B2 (tr) |
| DD (1) | DD125683A5 (tr) |
| DE (1) | DE2512177A1 (tr) |
| DK (1) | DK121476A (tr) |
| EG (1) | EG12366A (tr) |
| ES (1) | ES446181A1 (tr) |
| FI (1) | FI760723A (tr) |
| FR (1) | FR2304616A1 (tr) |
| GB (1) | GB1501786A (tr) |
| GR (1) | GR59318B (tr) |
| HU (1) | HU173955B (tr) |
| IE (1) | IE42660B1 (tr) |
| IL (1) | IL49230A (tr) |
| KE (1) | KE2872A (tr) |
| LU (1) | LU74593A1 (tr) |
| MY (1) | MY7800372A (tr) |
| NL (1) | NL7602928A (tr) |
| NO (1) | NO760777L (tr) |
| OA (1) | OA05276A (tr) |
| PL (1) | PL100904B1 (tr) |
| PT (1) | PT64914B (tr) |
| RO (1) | RO69116A (tr) |
| SE (1) | SE7602119L (tr) |
| SU (1) | SU569292A3 (tr) |
| TR (1) | TR18869A (tr) |
| ZA (1) | ZA761709B (tr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2636786A1 (de) * | 1976-08-16 | 1978-02-23 | Bayer Ag | Verfahren zur herstellung von o,o-dimethyl-o-(2,2-dichlorvinyl) -thionophosphorsaeureester |
| US7576301B2 (en) | 2004-09-28 | 2009-08-18 | Freegen Research Limited | Building incorporating a thermal insulation assembly and method of conserving energy |
-
1975
- 1975-03-19 ZA ZA761709A patent/ZA761709B/xx unknown
- 1975-03-20 DE DE19752512177 patent/DE2512177A1/de active Pending
-
1976
- 1976-02-20 DD DD191392A patent/DD125683A5/xx unknown
- 1976-02-23 SE SE7602119A patent/SE7602119L/xx unknown
- 1976-03-05 NO NO760777A patent/NO760777L/no unknown
- 1976-03-11 AU AU11853/76A patent/AU504691B2/en not_active Expired
- 1976-03-15 SU SU7602333904A patent/SU569292A3/ru active
- 1976-03-16 CH CH328676A patent/CH601330A5/xx not_active IP Right Cessation
- 1976-03-16 BG BG032622A patent/BG27237A3/xx unknown
- 1976-03-17 PT PT64914A patent/PT64914B/pt unknown
- 1976-03-17 IL IL49230A patent/IL49230A/xx unknown
- 1976-03-17 EG EG161/76A patent/EG12366A/xx active
- 1976-03-18 JP JP51028679A patent/JPS51115422A/ja active Pending
- 1976-03-18 GR GR50345A patent/GR59318B/el unknown
- 1976-03-18 BE BE165284A patent/BE839712A/xx unknown
- 1976-03-18 LU LU74593A patent/LU74593A1/xx unknown
- 1976-03-18 PL PL1976188056A patent/PL100904B1/pl unknown
- 1976-03-18 AT AT201876A patent/AT338289B/de not_active IP Right Cessation
- 1976-03-18 FI FI760723A patent/FI760723A/fi not_active Application Discontinuation
- 1976-03-18 RO RO7685200A patent/RO69116A/ro unknown
- 1976-03-18 ES ES446181A patent/ES446181A1/es not_active Expired
- 1976-03-19 NL NL7602928A patent/NL7602928A/xx not_active Application Discontinuation
- 1976-03-19 FR FR7607938A patent/FR2304616A1/fr active Granted
- 1976-03-19 GB GB11163/76A patent/GB1501786A/en not_active Expired
- 1976-03-19 OA OA55771A patent/OA05276A/xx unknown
- 1976-03-19 IE IE579/76A patent/IE42660B1/en unknown
- 1976-03-19 HU HU76BA3386A patent/HU173955B/hu unknown
- 1976-03-19 CA CA248,209A patent/CA1058631A/en not_active Expired
- 1976-03-19 TR TR18869A patent/TR18869A/tr unknown
- 1976-03-19 CS CS761798A patent/CS191211B2/cs unknown
- 1976-03-19 BR BR7601678A patent/BR7601678A/pt unknown
- 1976-03-19 DK DK121476A patent/DK121476A/da unknown
-
1978
- 1978-08-10 KE KE2872A patent/KE2872A/xx unknown
- 1978-12-30 MY MY372/78A patent/MY7800372A/xx unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3652742A (en) | 2 2-dichloro-vinylphosphoric acid ester amides | |
| US3801679A (en) | N-(dimethylaminomethylidene)thiol-(thiono)-phosphoric acid ester imides s | |
| US3697518A (en) | Phosphorus acid esters of 3-hydroxy-benzo-1,2,4-triazine -1-n-oxide | |
| US3825557A (en) | O-(1-substituted-3-methyl-4-chloropyrazolo)-thionophosphoric(phosphonic)acid esters | |
| US3775517A (en) | 1-phenyl-2-cyano-2-methylvinyl-thiono-phosphoric(phosphonic)acid esters | |
| IL47958A (en) | Pyrimidinylthionophosphonic acid esters process for their preparation and insecticidal acaricidal and nematicidal compositions containing them | |
| US4104377A (en) | Disubstituted-O-(1-fluoro-2-halogenoethyl)-phosphoric(phosphonic) acid esters, and method of combating insects | |
| IE42660B1 (en) | Process for the preparation of the 0,0-dimethyl-0-(2,2-dichlorovinyl) ester and the 0,0-diethyl-0-(2,2-dichlorovinyl) ester of thionophosphoric acid | |
| US3641223A (en) | S-(2-chloro-2-bromo-ethyl-(di)thio-phosphoric and phosphonic acid esters | |
| US3761479A (en) | O-pyrazolo-pyrimidine-(thiono)-phosphoric (phosphonic) acid esters | |
| US3773861A (en) | O-phenyl-n-alkoxy-(thiono)-phosphoric(phosphonic) acid ester amides | |
| US4123478A (en) | Preparation of O, O-dimethyl-O-(2,2-dichlorovinyl)-thionophosphoric acid ester | |
| US3763285A (en) | 1-phenyl-2-cyanovinyl(thio)-phosphoric or-phosphonic acid esters | |
| US3793407A (en) | O,s,n-tri-aliphatic hydrocarbon-thiono-thiolphosphoric acid ester amides | |
| US3723456A (en) | Pyrazolo-(thiono)phosphoric(phosphonic) acid esters | |
| US3626036A (en) | O-methyl-o-(2,2 dichloro-vinyl) phosphoric acid ester monochloride and method of preparation | |
| US3621082A (en) | Amido-thiono-phosphoric acid phenyl esters | |
| US3862268A (en) | O-alkyl-s-(carbamoyloxy-methyl)-(thiono) thiolphosphoric (phosphonic) acid esters | |
| US3828063A (en) | Benzisoxazolo(thiono)phosphoric(phosphonic)acid esters | |
| US3740427A (en) | Insecticidally active lower alkyl-substituted 2 - chloro - 2-thiono-1,3,2-dioxaphosphorinane | |
| US3706820A (en) | S-alkylmercaptomethylthiophosphoric or phosphonic acid esters | |
| US4013794A (en) | O-alkyl-s-alkyl-o-phenyl phosphates and insecticidal and acaricidal method of use | |
| US3743687A (en) | Lower alkyl-s-(1-bromopropyl-(2)-mercaptomethyl)-(thiono)thiolphosphoric or phosphonic acid esters | |
| US4000268A (en) | N,N-dimethyl-N'-[O-phenyl-(thiono)-alkane-phosphonyl]-formamidines | |
| US3862271A (en) | O-alkyl-(thiono) thiol-s-(s-alkylmercapto-s-benzylmercapto-methyl)-phosphoric (phosphonic) acid esters |